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It’s midday and my friend and I have gotten off at the wrong stop.

Chicago’s “El” train costs only $2.25 for one-way fares, and if used correctly (the key idea here) you can get anywhere. Landing in Chicago’s O’Hare International Airport, the visitor can simply jump on the El and glide into the city. With 106 miles of track and 24-hour-a-day service on the busiest lines, this rapid transit system has been voted one of the “seven wonders of Chicago.”

But we miss changing El lines. Now we’ve walked over a mile to our hotel, suitcases in hand, and thirst dominates our needs. The first pub shows its sign: Streeter's Tavern. We look at ourselves and know that we have arrived. This would become our local bar for the weekend.

We meet Chris, the bartender, who works two days a week at Streeter's and does stand-up comedy for the remainder. It’s immediately realized that he has no problem motivating his crowds to chuckle. A quote from him includes, “I’m young and appreciative,” when two Australian cougars were settling up the bill. Within minutes we feel like locals, and Chris talks to us as friends (but he is still appreciative of tips of course).

On the way to another bar (see a theme of the weekend?), we encounter our second character of the trip. But he is no comedian – James is all business. On a random street corner, we pass him and hear a, “Do you all wanna hear a song?” Enjoy the video.

And on the last day it is found: the city bus tour of all city bus tours. In summer months the Chicago Trolley and Double Decker Co., coachusa.com/chicagotrolley, offers not just one, but three tours in and around the city that visitors can take advantage of over a three-day period. I’ve never seen any bus tour in the world covering their city with such detail.

I’m soaking up the information and views from the signature bus tour when it is realized that I have around an hour to get to O’Hare for my return flight. I sadly need to leave my Chicago times…and quickly.

“Where is the nearest train station to catch the El?”

“Catch that bus on the corner.”

"We had no idea that the first Australian to play in the NBA (Luc Longley) would be on our initial El ride."

I see the bus, run to it, and just before the doors close I slide in with my one (thankfully) small travel bag. But I don’t have any cash on me, just credit cards that don’t work on city buses. The driver sees the it’s-never-too-early-to-panic expression on my face imagining a phone call to a few very annoyed people in San Diego.

“Don’t worry about it. Take a seat.”

I make my flight by a few minutes. It is the final touch to a beautifully unplanned weekend.

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